Arrange tomato slices in a single layer on a platter. Combine 1 tablespoon balsamic vinegar and honey in a small bowl, stirring with a whisk. Drizzle mixture evenly over tomato slices. Sprinkle with salt and black pepper; marinate 15 minutes.
Cut bell peppers in half lengthwise; discard seeds and membranes. Place pepper halves, skin sides up, on a foil-lined baking sheet; flatten with hand. Broil 10 minutes or until bell peppers are blackened. Place in a zip-top plastic bag; seal. Let stand 10 minutes. Peel and cut into 3/4-inch strips.
Combine 1 tablespoon balsamic vinegar, red wine vinegar, oil, and garlic in a medium bowl; stir well with a whisk. Add bell peppers and caperberries; toss gently to coat. Top tomato slices with bell pepper mixture.